This thesis explores how irony in architecture activates a space to create a dialog between the space and its occupants by breaking rules, incorporating culture, and creating ambiguity. With orthodox modernism, much of architecture has become formulaic and merely functional. Users of architecture become desensitized to a space once it has become formulaic. Irony refers to the incongruity between what is expected and what actually happens. This incongruity not only challenges our preconception and expectations but is also thought provoking, reestablishing a dialog between the space and its occupants that was lost among much of the orthodox modernist architecture. Through literature review and case studies of irony in various disciplines including art, architecture, product design, interior design, and branding, the findings reveal that irony engages users, provides them experiences that go beyond the everyday, and allows them to formulate their own story based on their repertoire of experiences.